Weston is a charming town located in Fairfield County, Connecticut, known for its serene natural landscapes, impressive architecture, and affluent community. The town offers a perfect balance between rural and urban living, making it a popular destination for those seeking a luxurious lifestyle.

Best choice of shopping

  1. The Weston Shops - a collection of boutique stores that offer a wide range of luxury items, including designer clothes, jewelry, and home decor.
  2. The Westport Country Playhouse - a cultural center that hosts various events throughout the year, including theater productions, concerts, and art exhibits.
  3. The Merritt Parkway - a scenic route that offers stunning views of the town's natural beauty and connects Weston to neighboring towns.
  4. The Shops at the Green - a shopping center that features a mix of high-end stores, gourmet restaurants, and specialty shops.
  5. The Weston Farmers Market - a weekly market that sells fresh produce, artisanal goods, and other locally sourced products.

Most luxurious hotels

  1. The Inn at Longshore - a boutique hotel that offers elegant guest rooms, an award-winning restaurant, and breathtaking views of the Long Island Sound.
  2. The Delamar Southport - a luxury hotel that features a spa, fine dining, and stylish accommodations.
  3. The Westport Inn - a historic hotel that combines old-world charm with modern amenities, including a fitness center, a pool, and a restaurant.
  4. The Westport Hotel - a chic and stylish hotel that offers comfortable accommodations, exceptional service, and an unbeatable location in the heart of downtown Weston.
  5. The Residence Inn Weston - a modern hotel that offers spacious suites, an indoor pool, and a complimentary breakfast.

For those looking for an excellent dining experience, Weston has a range of upscale restaurants that offer exquisite cuisine and a cozy atmosphere. Here are the 5 most luxurious restaurants in Weston:

  1. The Schoolhouse at Cannondale - a farm-to-table restaurant that serves innovative American cuisine using locally sourced ingredients.
  2. The Red Barn Restaurant - a classic New England-style restaurant that offers traditional dishes made with fresh, locally sourced ingredients.
  3. The Little Barn - a cozy gastropub that serves craft cocktails and delicious comfort food in a laid-back setting.
  4. The Gray Goose Cafe - a casual dining restaurant that offers a menu of classic American dishes, as well as vegetarian and gluten-free options.
  5. The Cottage - a charming restaurant that serves elevated New American cuisine in a rustic, romantic atmosphere.

World class Residences

  1. 25 Tannery Lane: This stunning estate sits on 6.31 acres and boasts over 13,000 square feet of living space. It features a grand two-story foyer, six en-suite bedrooms, an indoor pool, home theater, and a full gym.
  2. 23 Hidden Spring Road: This exceptional stone and shingle colonial is situated on 2.02 acres of beautifully landscaped property. The home features six bedrooms, a custom library, a home theater, and an outdoor pool with a waterfall.
  3. 20 Stonegate Lane: This magnificent stone and shingle colonial sits on 3.01 acres of meticulously landscaped property. The home boasts six bedrooms, a gourmet kitchen, a home theater, and a wine cellar.
  4. 60 Norfield Road: This stunning 1930s colonial has been completely renovated and features six bedrooms, a chef's kitchen, a home gym, and an outdoor pool with a spa.
  5. 5 Osborn Farm Road: This incredible home sits on over 4 acres of beautifully landscaped property and features six bedrooms, a grand two-story foyer, a custom home theater, and an outdoor pool with a waterfall.
Discover a stunning custom crafted luxury home, complete with a separate one bedroom guest pool house, that stands as an architecturally significant estate designed to be cherished.
$3,999,999
Courtesy of Redfin Corporation
Shortlisted for Living Space Americas in The International Design Architecture Awards 2025, this exceptional home with a gorgeous pool in a coveted Lower Weston location has garnered global attention.
$2,999,000
Courtesy of Coldwell Banker Realty
This exquisite custom estate with pool site on 4.
$2,999,000
Courtesy of Coldwell Banker Realty
Welcome Home to 32 Kettle Creek Road Where Effortless Elegance Redefines Luxury Living This impressive modern farmhouse features 5 6 bedrooms, 5.
$2,699,000
Courtesy of Camelot Real Estate
Located down a bucolic lane with the utmost privacy, this home is minutes to downtown Wilton and Westport.
$1,379,000
Courtesy of Higgins Group Real Estate
Travel down a private country lane to the end of the cul de sac and you have found your home !
$919,000
Courtesy of Camelot Real Estate
Once The Uppen Parish Schoolhouse, now the most stylish renovated antique house in town !
$1,075,000
Courtesy of Compass Connecticut, LLC
Tucked on a peaceful cul de sac in prime lower Weston, this contemporary gem is a rare find.
$1,700,000
Courtesy of Compass Connecticut, LLC
Situated on one of Lower Weston's most desirable cul de sacs, this beautifully maintained 4 bedroom, 2 bath home is an absolute gem !
$949,000
Courtesy of Sotheby's International Realty
Tranquil Contemporary Retreat on 2.
$870,000
Courtesy of Iron Gates Realty
Located in Lower Lower Weston and in move in condition for summertime enjoyment, this beautiful 4 bedroom, 2 full and 2 half bath Colonial is set on one of the ...
$1,395,000
Courtesy of The Riverside Realty Group
This stunning Colonial sits proudly on a beautifully landscaped 2 acre lot on the corner of Coley Drive, just over the Westport line in Lower Weston.
$2,200,000
Courtesy of Higgins Group Real Estate
One of the most desirable neighborhood streets in Weston is the setting for this much loved Colonial with a pool, fully renovated kitchen and picturesque acreage.
$1,695,000
Courtesy of Keller Williams Realty
Ideally set on 3. 62 acres of professionally manicured grounds in Weston, CT, this stunning 4 5 bdrm 2 2 bath colonial offers a blend of timeless architecture and modern ...
$1,299,000
Courtesy of The Riverside Realty Group
Step into timeless elegance with this newly renovated 4 bedroom, 3.
$1,595,000
Courtesy of The Bridge Realty Inc
Unique opportunity to renovate, build or develop.
$899,900
Courtesy of Coldwell Banker Realty
Great opportunity to own this centrally located 4 bedroom Colonial style home situated on 2 acre lot at beginning of a cul de sac !
$1,049,900
Courtesy of Carbutti & Co., Realtors
Imagine waking up every morning in your own slice of paradise.
$1,525,000
Courtesy of Berkshire Hathaway NE Prop.
Welcome to your dream retreat a custom designed contemporary masterpiece nestled in the heart of nature.
$1,200,000
Courtesy of Keller Williams Prestige Prop.
Timeless elegance meets modern versatility in this expanded residence set on 2 peaceful acres in lower Weston, bordering Westport.
$1,595,000
Courtesy of Berkshire Hathaway NE Prop.
PRICE IMPROVEMENT to 899, 000 Located in the picturesque town of Weston, Connecticut, 2 Kramer Lane is a charming Tudor style home with four bedrooms and two and a half ...
$899,000
Courtesy of Compass Connecticut, LLC
29 Bradley Road seamlessly blends timeless New England charm with modern day comforts, set against the backdrop of one of Connecticut's most picturesque 1000 acre nature preserves.
$1,649,000
Courtesy of Camelot Real Estate
This elegant, totally renovated colonial in sought after lower Weston cul de sac on Westport's border close to all ; in move in condition is a true show stopper !
$1,499,000
Courtesy of Coldwell Banker Realty
Tremendous opportunity in Weston for a special home plus 3 potential building lots !
$2,300,000
Courtesy of Coldwell Banker Realty
Tremendous opportunity in Weston for a charming home plus 3 potential building lots !
$2,300,000
Courtesy of Coldwell Banker Realty
Discover the ideal site for your dream home with this exceptional 2.
$459,000
Courtesy of Compass Connecticut, LLC
Luxury Convenience Stunning Home Just Minutes from Merritt Parkway !
$1,649,000
Courtesy of William Pitt Sotheby's Int'l
80 K Price Reduction ! Amazing Value !
$899,000
Courtesy of William Raveis Real Estate
Nestled in a serene and private setting, this stunning custom colonial offers the perfect blend of elegance and comfort.
$1,999,000
Courtesy of Coldwell Banker Realty
This spacious colonial home is nestled in the desirable Georgetown neighborhood of Weston.
$900,000
Courtesy of Coldwell Banker Realty
Spectacular open floor plan highlights this lovely updated 3 bedroom, 3 full bath Ranch in Lower Weston.
$1,150,000
Courtesy of William Raveis Real Estate
Experience the perfect blend of luxury, comfort and natural beauty in this unparalleled countryside escape on private cul de sac.
$2,190,000
Courtesy of Keller Williams Realty
Experience dramatic, modern living in this grand home with a glorious gunite pool exceptional architectural appeal.
$1,779,000
Courtesy of Coldwell Banker Realty
Wonderful 4BR Colonial Cape with loads of charm and natural light, just minutes from the shops and restaurants of Georgetown !
$649,000
Courtesy of Coldwell Banker Realty
Nestled on a quiet cul de sac in desirable Lower Weston, this exceptional 4 bedroom residence offers unparalleled privacy and a lifestyle of leisure.
$1,795,000
Courtesy of William Raveis Real Estate
3 Mayflower Lane offers a perfect blend of modern sophistication and timeless charm.
$2,300,000
Courtesy of Compass Connecticut, LLC
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